(2S,3aR,9aS)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-7-methyl-3-methylene-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one | 1256086-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (2S,3aR,9aS)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-7-methyl-3-methylene-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
• CAS: 1256086-89-1
• 化学式: C₂₇H₃₀N₂O₄Si
• 分子量: 474.632
• InChiKey: KYLXPJADMVHVQC-OYRHQHFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  sodium benzoate 、 (2S,3aR,9aS)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-7-methyl-3-methylene-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 在 苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以64%的产率得到(2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methylenetetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-d-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

  摘要：

  We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.071
• 作为产物：
  描述：

  1-((2S,3S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methylenetetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 以76%的产率得到(2S,3aR,9aS)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-7-methyl-3-methylene-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
  参考文献：
  名称：

  Synthesis and antiviral evaluation of α-d-2′,3′-didehydro-2′,3′-dideoxy-3′-C-hydroxymethyl nucleosides

  摘要：

  We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-alpha-nucleosides. By applying the method, we have synthesized alpha-D-2',3'-didehydro-2',3'-dideoxy- 3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.071